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Highly Emissive Chiral Lanthanide(Iii) Complexes for Labelling and Imaging

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Highly Emissive Chiral Lanthanide(Iii) Complexes for Labelling and Imaging Durham E-Theses HIGHLY EMISSIVE CHIRAL LANTHANIDE(III) COMPLEXES FOR LABELLING AND IMAGING FRAWLEY, ANDREW,TIMOTHY How to cite: FRAWLEY, ANDREW,TIMOTHY (2017) HIGHLY EMISSIVE CHIRAL LANTHANIDE(III) COMPLEXES FOR LABELLING AND IMAGING, Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/12423/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk 2 HIGHLY EMISSIVE CHIRAL LANTHANIDE(III) COMPLEXES FOR LABELLING AND IMAGING Andrew Timothy Frawley A thesis submitted for the degree of Doctor of Philosophy 2017 Declaration The work described herein was undertaken at the Department of Chemistry, Durham University between October 2014 and September 2017. All of the work is my own, except where specifically stated otherwise. No part has previously been submitted for a degree at this or any other university. Statement of Copyright The copyright of this thesis rests with the author. No quotation from it should be published without the author’s prior written consent and information derived from it should be acknowledged. i Abstract Sensitised lanthanide complexes based on macrocyclic chelating ligands have been used extensively to study biological function at a cellular level, due to their very bright and long-lived emission, sharp emission bands and high stability to photo- degradation. These photophysical properties, in addition to their excellent chiroptical behaviour, also make these complexes promising candidates for security labelling and as anti-counterfeiting tools. Novel highly emissive chiral europium(III) complexes based on macrocyclic ligands have been synthesised and their photophysical properties studied. They possess high molar extinction coefficients and are amenable to excitation using commonly available light sources. These complexes have been resolved by chiral HPLC and the circularly polarised luminescence (CPL) spectra of their enantiomers recorded. They exhibit strong circularly polarised emission in response to excitation using near ultra-violet light, and are stable to thermally-activated racemisation. A simple off-the-shelf camera set up has been developed which is capable of discriminating ‘real’ europium(III) emission from emission from a ‘fake’ marking, based on emission lifetime and wavelength. Additionally, chiroptical discrimination has been achieved using a custom built microscope incorporating a quarter-wave plate and linear polariser. The solvent dependent emission behaviour of a series of C3-symmetric lanthanide(III) complexes has been studied, demonstrating that the form of the total emission and CPL is extremely sensitive to minor changes in the outer solvation sphere of the complex. Finally, macropinocytosis has been identified as the mechanism of cell uptake of this family of complexes in NIH-3T3 cells, and the internalisation and subsequent sub-cellular localisation has been shown to be dependent on complex chirality. ii Acknowledgements I would like to thank the following people for making this work possible: My supervisor, Prof. David Parker, for giving me the opportunity to carry out this project and for his ideas, guidance and support over the last 4 years. Special thanks must go to Dr. Robert Pal for his help with all things both living and optical, specifically cameras, microscopes and cells. Thank you to the following members of the Chemistry Department for their assistance: Dr. Alan Kenwright, Dr. Juan Aguilar, Catherine Heffernan and Dr. Raquel Belda-Vidal for NMR spectroscopy; Dr. Jackie Mosely, Pete Stokes and Dr. Dave Parker for mass spectrometry; Dr. Aileen Congreve and Lenny Lauchlan for HPLC training and for letting me loose in the HPLC lab; Dr. Lars-Olof Pålsson for assistance with low temperature photophysical measurements; Annette Passmoor, Gary Southern and all the stores and technical team for keeping us supplied with equipment and chemicals; the lab attendants for the daily supply of tea and coffee, and specifically to Claire for gently encouraging me to tidy my desk every so often. Thanks also to Dr. Chris Ottley (Dept. of Earth Sciences) for ICP-MS analyses. Thanks to all the Parker Group members, past and present. In particular I’d like to thank Steve, Brian, Kanthi, Cidalia, Nicola, Matthieu, Kevin, Alex, Martina, Emily, Katie, Sergey, Edward, Alice, Laura, Ryan and Hannah for sharing their knowledge and keeping me going over the years. I would also like to acknowledge Durham University for the award of a Durham Doctoral Scholarship which has allowed me to pursue my postgraduate studies. Thanks to all the leaders, parents and young people at 19th Durham Scout Group for providing plenty of fun and adventure (and distraction from chemistry). A special thank you to Siân, Will, Evelyn and Nicholas Greeves for being my ‘Durham family’ for the last 7 years. I really can’t thank you enough for everything you’ve done. Finally, the biggest thanks to Mum, Dad and Helen for their unwavering support in everything I do. iii List of Abbreviations α1-AGP alpha-1-acid glycoprotein 12-N4 1,4,7,10-tetraazacyclododecane 9-N3 1,4,7-triazacyclononane A431 human epidermoid carcinoma cell line AAT alpha-1-antitrypsin AC alternating current acac acetylacetonate ADP adenosine diphosphate AFM atomic force microscopy AMP adenosine monophosphate ATP adenosine triphosphate bda 2,2’-bipyridine-6,6’-dicarboxylate BET back energy transfer BINAP 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl BINOL 1,1'-bi-2-naphthol BODIPY boron-dipyrromethene BP band pass br broad (NMR) BSA bovine serum albumin CCD charge-coupled device CCDC Cambridge Crystallographic Data Centre CD circular dichroism CHO Chinese hamster ovary CIE Commission internationale de l'éclairage (International Commission on Illumination) CPEL circularly polarised electroluminescence CPL circularly polarised luminescence CSP chiral stationary phase iv CW continuous wave cyclen 1,4,7,10-tetraazacyclododecane d, dd, ddd doublet, doublet of doublets, etc. (NMR) DC direct current DCM dichloromethane dfppy difluorophenylpyridine DFT density functional theory DMEM Dulbecco's modified Eagle's medium DMF N,N-dimethylformamide DMSO dimethylsulfoxide DOTA 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid dpa dipicolinic acid, pyridine-2,6-dicarboxylic acid dppf 1,1'-bis(diphenylphosphino)ferrocene dpyb 1,3-dipyridylbenzene DSLR digital single lens reflex DTPA diethylenetriaminepentaacetic acid ED electric dipole ee enantiomeric excess 푁 퐸푇 Reichardt's normalised solvent polarity eq. equivalents ESI electrospray ionisation eT electron transfer ET energy transfer facam 3-trifluoroacetylcamphorate FOV field of view FRET Förster/fluorescence resonance energy transfer FWHM full width half maximum GCMS gas chromatography mass spectrometry HEPES 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid hfac 1,1,1,5,5,5-hexafluoroacetylacetonate v hfbc 3-heptafluorobutyrylcamphorate HP-DO3A 10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7- triacetic acid HPLC high pressure/performance liquid chromatography HRMS high resolution mass spectrometry IC internal conversion IC50 half-maximal inhibitory concentration ICP-MS inductively coupled plasma mass spectrometry ICT internal charge transfer IR infra-red ISC intersystem crossing iTTL through the lens metering (camera flash unit) LCMS liquid chromatography mass spectrometry LED light emitting diode Ln lanthanide LP long pass LSCM laser scanning confocal microscopy LTG LysoTracker Green m multiplet (NMR) m.p. melting point mCPBA meta-chloroperbenzoic acid MD magnetic dipole MOPS 3-(N-morpholino)propanesulfonic acid MRI magnetic resonance imaging Ms methanesulfonyl MTG MitoTracker Green NIH-3T3 mouse skin fibroblast cell line NMR nuclear magnetic resonance NOTA 1,4,7-triazacyclononane-1,4,7-triacetic acid PBS phosphate buffered saline vi pda 1,10-phenanthroline-2,9-dicarboxylic acid PEM photoelastic modulator PET positron emission tomography phen phenanthroline PhMoNa phase modulated nanoscopy PMMA poly(methyl methacrylate) PMT photomultiplier tube ppm parts per million ppy phenylpyridine PVC poly(vinyl chloride) Q quencher QR quick response QToF quadrupole time of flight (mass spectrometry) S singlet (energy level) s singlet (NMR) SEM scanning electron microscopy SOM single organic molecule T triplet (energy level) t triplet (NMR) TBAF tetrabutylammonium fluoride td triplet of doublets (NMR) TFE 2,2,2-trifluoroethanol THF tetrahydrofuran TLC thin layer chromatography TQD triple quadrupole (mass spectrometry) TTA 2-thenoyltrifluoroacetonate UPLC ultra performance liquid chromatography UV ultra violet YAG yttrium aluminium garnet, Y3Al5O12 vii Table of Contents Abstract ........................................................................................................................ ii Acknowledgements ....................................................................................................
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